Sissy Jail Stories

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Orientation
Length
Source
Infinite Scroll

Lost Empire Ch. 13

by Pars001 on Sep 13, 2017
Non-Erotic

Derrick's heart had been hardened, the A.I.'s were more alive to him them almost all the humans he'd met were. After losing Lucy and instigating the installation of the new detection system, Derrick felt he was ready to start hunting the other EIG's. Then again he had the nagging thought in the back of his mind that he should hear the message Tempro had for...

A Cuck and Bull Story

by PBEnis on Jul 3, 2018
Loving Wives

It was around 10pm and my wife, Katie, and I were settling into our respective sides of the bed to what we refer to as "piddling for a while" which means play with our phones or computers before bedtime. She loves her phone, my thumbs are tired by the end of the day and I prefer the computer. I had headphones on for privacy but my laughter made her ask, "w...

Empty Nest Pt. 01

by CAROLINA_GENTLEMAN on Jun 5, 2019
Loving Wives

Annie sat on the bed, smiling up into his face, with Sam standing in front of her, she pulled his shirt from his pants, unbuttoned it and tossed it to the floor. She then began gently kissing his stomach and chest while Sam closed his eyes and moaned slightly. Slowly, she worked her way over to his right nipple and using just the tip of her tongue began lick...

The Flight

by Resonance2K on May 21, 2019
Erotic Couplings

This whole trip is likely my biggest fear manifest. I generally love to travel. I try to spend as few weekends in my apartment as I can in lieu of hopping on a plane for a quick two-day jaunt to any of the union's 48 continental states. But for each of those trips -- and for any trip I've taken anywhere, really -- I'm either traveling with someone, visitin...

A Chance Remark

by blackstroker on Jun 12, 2019
Anal

My neighbors were having money problems. The wife had lost her job over a year ago due to misappropriation of funds. She had been spared jail time after a settlement was made, and was now back to being just a housewife after failing to land another job. From conversations overheard, the husband was no longer getting the many hours of overtime he'd been enjoy...

A Long Time Coming... Pt. 03

by Jckpnsvg on Jan 14, 2019
Loving Wives

Morning came as morning does, the slow rise of the sun upon the eastern horizon, the gradual brightening of the day and the quickening of life to meet the day. My waking up was shocking, about 45 pounds of excited 4 year old landed on me in my sleep. For most people this might of been a near normal thing, but given my recent history, it almost scared me to...

Sort of Legal Ch. 12

by dididothat on Dec 17, 2018
Celebrities & Fan Fiction

Ginger sat on the seat as Megan stripped off and stood under the shower, with nothing else on her mind she watched Megan's tight ass jiggle as she washed herself. Carful of her dressings Ginger took off her own clothes. "Are you checking out my ass?" Megan asked as shampoo suds ran down her back and over the tight globes of her ass. "Sorry, I was miles...

Something about Me and You Pt. 03

by Erichmasterfield on Oct 7, 2019
Transgender & Crossdressers

Thank you for all of the kind words you all have expressed, I'm habitually excited to see that the reaction to part two was outstanding. At the time of writing this it scores 4.82 which places it in the top 100 overall in this category and the top 50 this year! I suppose in a long winded, kind of scatterbrain way, I want to say thank you. Now, I took a lot...

The RepAct Ch. 01

by goodwood71 on Sep 24, 2019
Sci-Fi & Fantasy

Disclaimer: This storyline is a fictitious account of a white married couple dealing with a reparations act being passed in a near future America. It will therefore delve into interracial cuckolding. If this is not your interest, please do not read this story and move on to a subject you prefer. For anyone still reading, I hope you will enjoy the following s...

Unicorn

by PAPATOAD on Oct 22, 2019
Loving Wives

This is a re-posting of a 2008 story that has been re-edited. ***** I always felt that I had a happy married life. I was pleased with how things were going and just naturally figured my wife, Kathy, felt the same way. I am a lawyer, to be more specific, a divorce lawyer. I graduated from law school about sixteen years ago. I started with a small law firm,...